Tackle England's greatest walking challenge on one of our tailored itineraries, with maps, guidebooks, cosy accommodation and daily luggage transfers included. The Pennine Way follows the spine of England on a trek of a lifetime through moorland and over rolling hills.

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Pennine Way

An iconic walking trail through the Peak District, Pennines, Yorkshire and Northumberland.

3 to 22 nights

20-256 miles

Moderate to Strenuous

From £260 per person

About The Trail

Britain’s first and best-known National Trail marches along the backbone of England, over gritstone moors, limestone pavement, peaty bogs and glaciated chasms. These wild landscapes mark the Pennine Way as one of the country’s most demanding long distance walks – and one of the most satisfying to complete.

This rising, falling route has its gentle moments, too. Through Swaledale, it tours farmland, crisscrossed by drystone walls; beside the River Tees, it sweeps through wildflower meadows; and from even the highest summits it finds its way into welcoming villages.

We offer multiple holiday options along this trail. If you wish to walk the entire trail, simply select the first option from the list below.

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when
choosing your holiday.

A short walking holiday through the stunning North Pennines from Middleton-in-Teesdale to Dufton.Find Out More

Customer reviews from the Pennine Way

“The B&B's were all excellent with very kind and friendly people. We thoroughly enjoyed our Pennine way walk and found the map book and guide book you sent useful. Thank you for the help and guidance, we would definitely recommend you to others.”

Mr Richardson, UK

“All the accommodation was good to excellent.”

Dr Thamia, UK

“Thank you vey much for everything - arrangements worked perfectly.”

Ms Cadwallader, UK

“The holiday was well-organised and the accommodation was of a high standard.”

Mrs Russell, UK

“Totally exhilarating and fulfilling walk through some stunning countryside. All pre travel information was detailed as was the guidebook and the accommodation details which assisted with daily planning. Baggage and taxi transfers all went smoothly and without any issues. We have used Contours on previous occasions and have no hesitation on using or recommending Contours.”

Mrs Davies, UK

“Our 5th Contours holiday and right up there with the best. Amazing scenery, open spaces, warm beds and friendly local people. And we only got soaked once! We really benefited from the rest day in the middle (clearly showing our age!) and would recommend to others who want to take on a challenging walk without overdoing it.”

Mrs Thurgood, UK

“Would recommend if anyone asked, it is a challenging walk but very enjoyable.”

Mr Clark, UK

“Thank you for the arrangements you made for our recent Pennine Way Walk. They all worked without any problems or difficulties and certainly added to the enjoyment of the walk. Our bags were at our next stop when we arrived, without exception we were greeted there with warmth and kindness and taxi drivers were expecting our calls when we made contact with them. Everywhere we stayed was comfortable, help was always available and generally our desire to make an early start was understood and accommodated by both the B&B/Hotel and the taxi service. All along our route we met friendly, kind and helpful people who added further enjoyment to our walk. We have been booking holidays with CWH for the last seven years and your arrangements have always worked well.”

Mr Duerden, UK

“Would recommend if anyone asked, it is a challenging walk but very enjoyable.”